Once a proud team in the Windy City, the Chicago White Sox are now rowing in seas so deep that even hope appears afraid to dip in. Guaranteed Rate Field has a different energy these days—less bustle, more uncertainty. Not the kind that comes from a last-minute pitching change or a tense ninth inning. This is the confusion that settles in when your team is 5-19; even spring’s hope seems to have packed up and left by April. Are the players to blame? Or is the owner at fault for not spending enough?

If baseball is a game of streaks, the White Sox have unfortunately chosen disappointment. Since Opening Day, they have recorded only four victories, accumulating losses at an alarming, historically significant rate. Their 41-121 record in 2024 was the lowest the league had seen in a season. And if you thought that was rock bottom, 2025 looks determined to show there’s still room to fall. Will the fans be getting another letter by the end of this season?

And this is when the whispers become shouts: supporters are not just exhausted—they’re fed up. Many feel that the fundamental problem is right at the top. Recently, a well-known figure in the Chicago sports scene, Jon Greenberg, voiced a growing sentiment. On Foul Territory, he bluntly said of Jerry Reinsdorf, “If he really cares for the fans and wants to make things better, as he said repeatedly, then he should see that it’s just time for him to go.”

Looking at the bigger picture, it’s hard to argue with that. The White Sox haven’t performed like a big-market team for years. Other clubs build dynasties with shrewd trades and outstanding drafts, but the White Sox have been caught in a cycle of underperformance and broken promises.

Even their largest financial commitment— Andrew Benintendi‘s 5-year, $75 million contract inked in 2022—is modest. Let that sink in. In contrast, other teams hand out $700 million like Halloween candy. The ChiSox spending: Crickets. Even though it’s his tough job for the manager to find positives in a terrible season, Will Venable stays optimistic. After yet another loss, he still managed to say, “A lot of good at-bats where we’re able to create some traffic.” He added, “We’ve just got to find a way to cash in. It’s as simple as that. Good, quality at-bats, and we just need to keep it going.” 

We’ve all heard that “money can’t buy happiness.” But in the case of the White Sox, it can certainly buy better baseball, and maybe even some wins, too.

White Sox’s historic struggles

The White Sox have been mired in an extended downturn, with their challenges laid bare in the 2024 and 2025 seasons. In their lowest record of 2024, the club set franchise records for losses both at home and on the road, and endured several long losing streaks, including a 21-game slump.

With just 3.07 runs per game and a collective .220/.278/. 339, the 2024 club ranked among the league’s least effective offensive teams. Their 76 OPS+ meant they were 24% below league average in offensive output. Posting a league-worst -83 total zone run, they demonstrated major defensive flaws.

Another source of worry was the bullpen, which had the lowest save rate in MLB—just 35%. With 37 blown saves, they led the league; their relievers ranked 29th with a 4.77 ERA. The bullpen also surrendered 82 home runs, second-most in the league, and issued 327 walks—the most in the majors.

The 2025 season has shown hardly any improvement. With a 5-19 record, the White Sox continue their pattern of underperformance. The team continues to struggle with persistent problems in pitching, defence, and clutch hitting, despite a management change. As they seek to rebuild and regain competitiveness, the franchise faces a difficult road ahead. Will Reinsdorf sell the team, or will he finally start writing some checks?